A7486

Adapalene

≥98% (HPLC)

• Synonyme(s) : 6-(4-Methoxy-3-tricyclo[3.3.1.1^3,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid, 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid, CD-271, Differin
• Formule empirique (notation de Hill): C₂₈H₂₈O₃
• Numéro CAS: 106685-40-9
• Poids moléculaire : 412.52
• Numéro MDL: MFCD03106112
• Code UNSPSC : 12352200
• ID de substance PubChem : 329770932
• Nomenclature NACRES : NA.77

Propriétés

• Niveau de qualité: 100
• Pureté: ≥98% (HPLC)
• Forme: powder
• Conditions de stockage: desiccated
• Couleur: white to off-white
• Solubilité: DMSO: >10 mg/mL
• Température de stockage: 2-8°C
• Chaîne SMILES: COc1ccc(cc1C23C[C@H]4C[C@H](C[C@H](C4)C2)C3)-c5ccc6cc(ccc6c5)C(O)=O
• InChI: 1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)/t17-,18+,19-,28-
• Clé InChI: LZCDAPDGXCYOEH-AADAIPAGSA-N

Description

Application

Adapalen has been used as a supplement during culturing of peripheral blood mononuclear cells (PBMC).

Adapalene has been used as a retinoic acid receptor (RAR) agonist to study its effects on inhibiting transcription of hepatitis B virus in covalently closed circular DNA (cccDNA). It has also been used as a component to culture mixed lymphocyte reactions (MLR) to study its effects on isolated macrophages.

Actions biochimiques/physiologiques

Adapalene is a synthetic derivative of naphthoic acid. It possesses retinoid activity. Adapalene is involved in regulating cellular keratinization and inflammatory process.

Adapalene, also referred as Differin, is a derivative of naphthoic acid. It is widely used for topical treatment of acne vulgaris. Adapalene elicits anti-inflammatory and retinoid-like activity. It also has a potential to regulate keratinization and differentiation of follicular epithelial cells.

Retinoic acid analogue that is a RARβ and RARγ agonist (AC50 values are 2.2, 9.3, 22 and > 1000 nM for RARβ, RARγ, RARα and RXRα receptors respectively). Inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro. Displays comedolytic activity. Its unique pharmacological properties make it superior to other retinoids for the treatment of acne.

Caractéristiques et avantages

This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Informations sur la sécurité

• Pictogrammes: GHS08
• Mention d'avertissement: Warning
• Mentions de danger: H361d
• Conseils de prudence: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Classification des risques: Repr. 2
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable